Arsenal suffered a shock Europa League exit to Olympiakos Piraeus on away goals after a 2-1 extra-time home defeat, while Manchester United and Wolverhampton Wanderers cruised into the last 16 with emphatic aggregate wins on Thursday.
The North London club were among several heavyweights who slumped out as the Portuguese trio of Benfica, Sporting and Porto as well as Ajax Amsterdam and Celtic were also eliminated from Europe’s second-tier competition in the Round of 32.
Arsenal had beaten Olympiakos 1-0 in the first leg and appeared to have done enough to squeeze through when Pierre-Emerick Aubameyang struck in the 113th minute to cancel out Pape Cisse’s 53rd-minute header which levelled the tie on aggregate.
But the visitors had the last laugh as Youssef El Arabi struck seven minutes later to delight the noisy contingent of away fans, with Aubameyang missing a gilt-edged chance to force another twist with the last kick of the game.
Manchester United breezed to a 6-1 aggregate win over 10-man Bruges after a 5-0 return-leg rout of the Belgians at Old Trafford, while Wolves advanced with a 6-3 overall victory against Espanyol despite a 3-2 second-leg defeat in Spain.
New loan signing Odion Ighalo celebrated his first start for United with his maiden goal for the club after Bruno Fernandes had fired the home side ahead with a 27th-minute penalty which also produced a red card for Bruges defender Simon Deli.
The centre back was dismissed after he dived in goalkeeping fashion to handle a Daniel James shot before Fernandes sent Simon Mignolet the wrong way with the spot-kick.
Scot McTominay made it 3-0 on the night with a fine first-time shot from 18 metres just before the break and Brazilian midfielder Fred put the icing on the cake with a late brace for United, who won Europe’s second-tier competition in 2016.
Wolves took a 4-0 first-leg lead to Espanyol and never looked in danger as Adama Traore scrambled in a close-range effort and Matt Doherty also scored as they twice cancelled out goals from Jonathan Calleri who scored a hat-trick.